6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside | 110101-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside
• 英文别名: N-acetyl-D-galactosamine；6-aminohexyl β-N-acetylgalactosamine；6-Aminohexyl 2-acetamido-2-deoxy-beta-d-galactopyranoside；N-[(2R,3R,4R,5R,6R)-2-(6-aminohexoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 110101-40-1
• 化学式: C₁₄H₂₈N₂O₆
• 分子量: 320.386
• InChiKey: BYQGHEVGCGGHPF-RKQHYHRCSA-N

物化性质

• 沸点：
  593.6±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  134
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside 在 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 G-ah-GalNAc
  参考文献：
  名称：

  New and more efficient multivalent glyco-ligands for asialoglycoprotein receptor of mammalian hepatocytes

  摘要：

  New multi-valent, carbohydrate ligands that contain terminal N-acetylgalactosamine (GalNAc) or lactose (Lac) were prepared using a nitrilotriacetic acid (NTA) derivative of L-lysine as scaffold. Tri-valent structures were prepared by attaching an x-amino glycoside of GalNAc or Lac to each of the three carboxyl groups of N-epsilon-protected N-alpha-dicarboxymethyl-L-lysine. In addition, a hexa-valent lactoside was synthesized by attaching N-epsilon-deprotected trivalent lactoside to each of the carboxyl group of N-alpha-(trifluoroacetamido) hexanoyl L-aspartic acid. Tri-valent GalNAc glycosides and the hexa-valent lactoside had high affinity (dissociation constants approaching nM) for rat hepatocytes. The hexa-valent lactoside, after de-Ne-protection, was modified with a chelator, diethylenetriaminepentaacetic acid (DTPA), through which a fluorescent or radioactive tag, such as europium or indium, can be firmly attached. Intravenous infusion of (111)Indium-tagged hexa-valent lactoside to rats and mice resulted in nearly exclusive accumulation of radioactivity in the liver.(C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.027
• 作为产物：
  描述：

  6-溴正己醇 在 palladium on activated charcoal sodium azide 、 三氟甲磺酸三甲基硅酯 、 氢气 、 溶剂黄146 、 甲胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-aminohexyl 2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  一种新的同双功能对硝基苯基酯偶联剂，用于制备新糖蛋白。

  摘要：

  已经设计了新的接头系统并将其应用于新糖蛋白合成。寡糖ω-氨基烷基糖苷与同双功能的己二酸对硝基苯基二酯在干燥的DMF中反应，可得到相应的酰胺半酯，收率高，稳定性好，可进行色谱纯化。随后在非常温和的条件下与牛血清白蛋白结合，可以有效地提供相应的新糖蛋白。该方法非常适合于极少量（mg）的寡糖和蛋白质的偶联。[结构：见文字]

  DOI：

  10.1021/ol048614m

文献信息

• NOVEL LIVER-TARGETING AGENTS AND THEIR SYNTHESIS
  申请人：LEE REIKO TAKASAKA

  公开号：US20110077386A1

  公开（公告）日：2011-03-31

  This invention provides novel liver targeting agents and their synthetic methods. A liver targeting agent, with a lysine based nitrilo triacetic acid structure as backbone which acquires multivalency with saccharide groups, to bind with a galactosamine chain or lactose chain is disclosed. In particular, only one amino acid L-lysine is involved to provide trivalency. All carboxyl groups in N ε -benzyloxycarbonyl-N α -dicarboxymethyl-L-lysine can be conjugated with three glycosides of ahGalNAc or ahLac in one step. This invention also provides a hexa-lactoside. In particular, the TFA-AHA-Asp was used to conjugate 2 moles of NTA(ahLac) 3 . This invention also provides a method for adding a spacer between NTA and DTPA. The extended hepatocyte-specific glyco-ligand has higher 111 In-radiolabelling yield than those non-extended.

  该发明提供了新型的肝靶向药物及其合成方法。一种肝靶向药物，以赖氨酸为骨架，具有氨基三乙酸结构，通过与糖苷基团形成多价性，与半乳糖胺链或乳糖链结合。具体来说，仅涉及一种氨基酸L-赖氨酸，以提供三价性。Nε-苄氧羰基-Nα-二羧甲基-L-赖氨酸中的所有羧基可以在一步中与三个ahGalNAc或ahLac的糖苷结合。该发明还提供了一种六乳糖苷。具体来说，TFA-AHA-Asp被用于将2摩尔的NTA(ahLac)3结合。该发明还提供了一种在NTA和DTPA之间添加间隔物的方法。扩展的肝细胞特异性糖基配体的111In标记产率高于非扩展的配体。
• New and more efficient multivalent glyco-ligands for asialoglycoprotein receptor of mammalian hepatocytes
  作者：Reiko T. Lee、Mei-Hui Wang、Wuu-Jyh Lin、Yuan C. Lee

  DOI：10.1016/j.bmc.2011.03.027

  日期：2011.4

  New multi-valent, carbohydrate ligands that contain terminal N-acetylgalactosamine (GalNAc) or lactose (Lac) were prepared using a nitrilotriacetic acid (NTA) derivative of L-lysine as scaffold. Tri-valent structures were prepared by attaching an x-amino glycoside of GalNAc or Lac to each of the three carboxyl groups of N-epsilon-protected N-alpha-dicarboxymethyl-L-lysine. In addition, a hexa-valent lactoside was synthesized by attaching N-epsilon-deprotected trivalent lactoside to each of the carboxyl group of N-alpha-(trifluoroacetamido) hexanoyl L-aspartic acid. Tri-valent GalNAc glycosides and the hexa-valent lactoside had high affinity (dissociation constants approaching nM) for rat hepatocytes. The hexa-valent lactoside, after de-Ne-protection, was modified with a chelator, diethylenetriaminepentaacetic acid (DTPA), through which a fluorescent or radioactive tag, such as europium or indium, can be firmly attached. Intravenous infusion of (111)Indium-tagged hexa-valent lactoside to rats and mice resulted in nearly exclusive accumulation of radioactivity in the liver.(C) 2011 Elsevier Ltd. All rights reserved.
• A New Homobifunctional <i>p</i>-Nitro Phenyl Ester Coupling Reagent for the Preparation of Neoglycoproteins
  作者：Xiangyang Wu、Chang-Chun Ling、David R. Bundle

  DOI：10.1021/ol048614m

  日期：2004.11.1

  A new linker system has been designed and applied to neoglycoprotein synthesis. Reaction of oligosaccharide omega-aminoalkyl glycosides with homobifunctional adipic acid p-nitrophenyl diesters in dry DMF gave the corresponding amide half ester in good yields and of sufficient stability to permit chromatographic purification. Subsequent conjugation with bovine serum albumin under very mild conditions

  已经设计了新的接头系统并将其应用于新糖蛋白合成。寡糖ω-氨基烷基糖苷与同双功能的己二酸对硝基苯基二酯在干燥的DMF中反应，可得到相应的酰胺半酯，收率高，稳定性好，可进行色谱纯化。随后在非常温和的条件下与牛血清白蛋白结合，可以有效地提供相应的新糖蛋白。该方法非常适合于极少量（mg）的寡糖和蛋白质的偶联。[结构：见文字]